Chinese Journal of Organic Chemistry >
Asymmetric Synthesis of Hamaudol and sec-O-Glucosylhamaudol in Saposhnikovia divaricata (Turcz.) Schischk
Received date: 2024-03-04
Revised date: 2024-04-15
Online published: 2024-05-17
Supported by
National Natural Science Foundation of China(22271195); National Natural Science Foundation of China(22301185); Science and Technology Commission of Shanghai Municipality(21ZR1482100); Science and Technology Commission of Shanghai Municipality(22ZR1458900); Shanghai Science and Technology Development Fund from Central Leading Local Government(YDZX20223100001004); Organizational Key R&D Program of Shanghai University of Traditional Chinese Medicine(2023YZZ01); Expenditure Budget Program of Shanghai University of Traditional Chinese Medicine(2021LK001)
Chromones from the traditional Chinese medicine Saposhnikovia divaricata (Turcz.) Schischk exhibit various biological activities, among which the representative compounds, hamaudol and sec-O-glucosylhamaudol, have anti-allergic and anti-inflammatory activities. A concise asymmetric synthesis of hamaudol and sec-O-glucosylhamaudol has been accomplished. The key strategies included the Ca(OH)2-catalyzed regioselective construction of 6/6/6 tricyclic skeleton by aldol reaction/annulation of phenolic enolate with 3-methyl-2-butenal and the construction of chiral centers in the 3'-position by Jacobsen's asymmetric epoxidation reaction. This strategy provided a concise and rapid approach to synthesize hamaudol (linear 6-steps and 21% overall yield) and sec-O-glucosylhamaudol (linear 8-steps and 15% overall yield) from the commercial reagent.
Tao Zeng , Shusheng Zhang , Jianguo Fu , Chenguo Feng . Asymmetric Synthesis of Hamaudol and sec-O-Glucosylhamaudol in Saposhnikovia divaricata (Turcz.) Schischk[J]. Chinese Journal of Organic Chemistry, 2024 , 44(9) : 2862 -2868 . DOI: 10.6023/cjoc202403006
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